Patent GB-404794-A (GB)
Title: Manufacture of ortho-aminoaryl-alkylsulphones, ortho-aminoarylaralkylsulphones and azo-dyestuffs therefrom
IPC: C09B29/20
Filed: 1932-11-24
Abstract: Azo dyes insoluble in water are made on the fibre by coupling diazotised o-aminoarylalkylor aralkylsulphones or derivatives thereof with an arylide of 2 : 3-oxynaphthoic acid.  Orange shades fast to ironing are obtained.  In examples the following dyes are formed on cotton 5 1 - aminophenyl - 2 - methylsulphone --> the 2 - methyl - 4 - chloranilide, (6) 1-amino-5-trifluoromethylphenyl-2-methylsulphone --> the p-anisidide.  In a table the shades obtained by use of the following additional components are given: diazo components:--1-aminophenyl-2-ethylsulphone, 1-amino-5-chlorphenyl-2-methylor ethyl- or n-butyl- or benzylsulphone, 1-aminophenyl - 2 - n - butylsulphone, 1 - aminophenyl - 2 - benzylsulphone, 2 - aminonaphthyl - 1 - methylsulphone, 1 - amino - 4 - chlorphenyl - 2 - methylsulphone, 1 - amino - 5 - methylphenyl - 2 - methyl- or ethyl- or n-butyl- or benzylsulphone, 1 - amino - 5 - trifluoromethylphenyl-2 - ethylsulphone, 1 - amino - 5 - chlorophenyl - 2 - (4<1> - methylbenzylsulphone), 1 - aminophenyl - 2 - (4<1> - methylbenzylsulphone), 1 - aminophenyl - 2 - (3<1> : 4<1> - dichlorobenzylsulphone) and 1 - amino - 2 - methylsulphonylbenzene - 5 - sulphonic acid - dimethylamide: coupling components:--the b -naphthalide, 2 - methoxy - 4 - or 5 - chloranilide, o - anisidide, p-chloranilide, o- and p-toluidide, anilide, 2-methyl - 5 - chloranilide and 2 - methyl - 4 - methoxyanilide of 2 : 3-oxynaphthoic acid.  Specifications 6379/12, [Class 2 (iii), Dyes &c.], 17279/13, 279,146, [both in p  Class 15 (ii), Dyeing, Processes &c. for], and 361,097 are referred to.  o - Nitro and o - amino - arylalkyl - or aralkylsulphones are made by heating respectively in an aqueous weakly alkaline solution, an alkali metal salt of an a -(o-nitroarylsulphonyl) fatty acid or an a -(o-nitroarylsulphonyl)-aryl fatty acid and reducing.  In examples: (1) 4-chloro-2-nitrophenylsulphonylacetic acid is refluxed with aqueous sodium carbonate yielding 4-chloro-2-nitrophenylmethylsulphone which is reduced to the corresponding amino compound; (2) 4-chlor-2-nitrophenylthioglycollic acid is oxidised with potassium permanganate in presence of carbon dioxide to 4-chloro-2-nitrophenylsulphonylacetic acid which is treated as above; (3) 4-trifluoromethyl-2-nitrophenylsulphonylacetic acid is converted into 4-trifluoromethyl-2-nitrophenylsulphone as above and the latter is reduced; (4) a -(4-chloro-2-nitrophenylsulphonyl)-phenylacetic acid similarly yields 4-chloro-2-nitrophenylbenzylsulphone which is converted into the corresponding amino compound.  The following sulphones are also specified: 2-nitro- and aminophenylmethylor ethylsulphone, 4-chloro-2-nitro- and aminophenyl - n - propylsulphone, 2 - nitro- and aminophenylbenzylsulphone, 2 - aminophenyl - n - butylsulphone, 2 - aminophenylcyclohexylsulphone, 4 - chloro - 2 - nitro - and aminophenylethylsulphone, 4 - chloro - 2 - aminophenyl - n - butylsulphone, 5 - chlor - 2 - aminophenylmethylsulphone, 2 - aminonaphthyl - 1 - methylsulphone, 4 - methyl - 2 - nitro - and aminophenylmethyl- or ethyl sulphone, 4-methyl 2 - aminophenyl - n - butylsulphone, 4 - methyl - 2 - nitro - and aminophenylbenzylsulphone, 5 - methoxy - 2 - aminophenylmethylsulphone, 4 - or 5 - nitro - 2 - aminophenyl - methylsulphone, 4 - trifluoromethyl - 2 - nitro - and aminophenylethyl - or benzyl sulphone, 3 - nitro - and 3 - amino - 4 - methylsulphonylbenzenesulphonic acid - dimethylamide, 4 - chloro - 2 - nitro - and 2 - aminophenyl - (4<1> - methylbenzyl) - sulphone, 2 - nitro - and 2 - aminophenyl - (4<1> - methylbenzyl) - sulphone, 2 - nitro - and 2 - amino - phenyl - (3 : 4<1> - dichlorobenzyl)-sulphone.